(1R)-1-phenylethan-1-amine

• ChemBase ID: 69357
• Molecular Formular: C8H11N
• Molecular Mass: 121.17964
• Monoisotopic Mass: 121.08914936
• SMILES: [C@@H](C)(c1ccccc1)N
• Canonical SMILES: C[C@H](c1ccccc1)N
• InChI: InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m1/s1
• InChIKey: RQEUFEKYXDPUSK-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-phenylethan-1-amine
• IUPAC Traditional name: D-α-methylbenzylamine
• Synonyms: (1R)-1-phenylethan-1-amine; D-(+)-alpha-Methylbenzylamine; (R)-(+)-1-Phenylethylamine; (R)-1-Phenylethanamine; (R)-(+)-1-Phenylethylamine; (R)-(+)-α-Methylbenzylamine; (αR)-α-Methyl-benzenemethanamine; (+)-α-Phenethylamine; (R)-1-Amino-1-phenylethane; (R)-(+)-α-Methylbenzylamine; (αS)-α-Methyl-benzenemethanamine; (-)-α-Phenethylamine; (S)-1-Amino-1-phenylethane; (S)-(-)-α-Methylbenzylamine; (R)-(+)-1-苯基乙胺; (R)-(+)-1-苯乙胺; (R)-(+)-α-甲基苄胺

Database IDs

• CAS Number: 2627-86-3; 3886-69-9
• EC Number: 223-423-4
• MDL Number: MFCD00064405
• Beilstein Number: 2410916
• Merck Index: 146026
• PubChem SID: 24847222; 162035083; 24887139; 24887140
• PubChem CID: 643189

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.491073
• LogD (pH = 7.4): -0.7418205
• Log P: 1.5155892
• Molar Refractivity: 38.9502 cm^3
• Polarizability: 15.59687 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Ethyl Acetate
• Apperance: Colourless Liquid
• Melting Point: -10°C
• Boiling Point: 180-181°C; 187°C; 187-189 °C(lit.)
• Flash Point: 158 °F; 70 °C; 71°C(159°F)
• Density: 0.948; 0.952 g/mL at 20 °C(lit.)
• Refractive Index: 1.5260; n20/D 1.526(lit.); n20/D 1.528
• Vapor Pressure: 0.5 mmHg ( 20 °C)
• Optical Rotation: [α]20/D +30±1°, c = 10% in ethanol; [α]20/D +30±2°, c = 10% in ethanol; [α]23/D +38°, neat; +29 (c=10 in ethanol); +30 (c=10 in ethanol)
• Hydrophobicity(logP): 1.403

Safety Information

• Storage Condition: -20°C Freezer; Refrigerator
• Storage Warning: Air Sensitive; IRRITANT
• European Hazard Symbols: Corrosive (C); X
• UN Number: 2735; UN2735
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II; III
• Risk Statements: 21/22-34
• Safety Statements: 20-23-26-36/37/39-45-60; 26-28-36/37/39-45; 26-36/37/39-45-60
• TSCA Listed: false; 是
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H314-H318-H227; H302 + H312-H314
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2735 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); ≥99.0%; ≥99.0% (GC); ≥99.0% (sum of enantiomers, GC); 95%; 95+%; 98%; ChiPros 99+%, ee 99+%
• Grade: for chiral derivatization; produced by BASF; purum
• Optical Purity: ee: 96% (GLC); enantiomeric excess: ≥98.0%; enantiomeric ratio: ≥97:3 (GC); enantiomeric ratio: ≥99.5:0.5 (GC)
• Linear Formula: C6H5CH(CH3)NH2

DETAILS

Sigma Aldrich - 115541

Packaging
10, 25, 100 mL in glass bottle

Sigma Aldrich - 726621

Packaging
100, 500 g in glass bottle
Legal Information
ChiPros is a registered trademark of BASF SE

Sigma Aldrich - 77880

Other Notes
Standard chiral amine used for the resolution of acids. Use as chiral auxiliary1,2,3,4,5

Sigma Aldrich - 77879

Other Notes
Chiral amine used for the determination of the enantiomeric purity of acids1,2

REFERENCES

• For use in the enantioselective synthesis of ɑ-amino nitriles and amino acids in the Strecker reaction, see: Chem. Ber., 110, 2098 (1977); J. Org. Chem., 48, 5369 (1983). Similarly, the preformed imines can be reacted with Trimethylsilyl cyanide, A19598: Chem. Lett., 331, 737 (1975). Enantioselective synthesis of cyclohexylamines from 2-alkylcyclohexanones via the imine and reduction: Tetrahedron Lett., 22, 2633 (1981); Chem. Ber., 117, 2076 (1984). Enantioselective synthesis of ɑ-aminoacetals from 1,1-dialkoxy-2-propanones: Synthesis, 608 (1989).
• Both enantiomers are widely used resolving agent for chiral acids. They also find extensive use as chiral auxiliaries in asymmetric synthesis: